The skill I’m hiring for in 2025 as a CEO

It's not AI

👋 Hi, it's Greg and Taylor. Welcome to our newsletter on everything you wish your CEO told you about how to get ahead.

We have made our plan for the last 9 quarters at Section, since we made our AI pivot. From my perspective, we had no choice – to rebuild the confidence of the team, the board, and even myself. Making plan includes growing our enterprise business 100% this year, and so far we are on track.

But what has shocked me – and I do mean shock – is that how we are making the plan is not what I expected, even six months ago. The products, the pricing, the positioning, the people (employees and contractors) are NOT what we initially planned or what I expected.

Let me give you an example: We just hired a guy straight out of undergrad into a critical position (and they’re all critical, because we’re a 30-person team).

A year ago, I wouldn’t have hired him – I would have looked for an MBA with 5+ years of experience. In fact, I would not have even considered him. But he’s smart, he’s AI-native, and in the interview process, he convinced us his lack of experience would be compensated by his “AI-first” problem solving.

In my 30+ years, working in and leading startups, I have never experienced this rate of uncertainty and change – and opportunity.

Most days, I love it. Some days, my head spins and I struggle to keep up.

Saying “I’ve done this before” doesn’t go far these days because no one has done this before. The tried-and-true business models, marketing channels, pricing strategies, etc. will be transformed by AI, and our playbooks will be of little value. Your judgement will still have value - but you will have to learn to bring that judgement quickly and without prejudice for “how it used to be done”.

In this environment, the most valuable skill isn't technical expertise or even raw intelligence (though both help). It's your ability to absorb and react to change. Here’s how to do it.

Greg

Absorbing change matters more than ever

I think about hiring very differently now. And when I say now, I mean in the last six months – yes, what I value in new employees has changed that quickly. When I evaluate someone now, I'm looking for three specific change capabilities:

1. Raw mental agility. I want people who can move quickly between contexts without getting stuck. Mental horsepower matters when everything is shifting. I’m thinking about implementing something like the CCAT cognitive assessment in hiring as a baseline. And we are going to change our interview assignment process - to give people less time to come up with their answers. When you’re moving fast, you simply need people who think quickly.

2. Emotional resilience. We all talk about resilience, but it's hard to interview for. What I'm really looking for is someone who doesn't freak out when things change. Asking for time to figure it out is fine. Not loving every change is normal. But freakouts are unproductive and distracting. I need people with a really fast turnaround to change – a short window to absorb it and move forward.

3. Speed of response. This is the big one. I want people who can hear about a change, take a few hours to think about it, and then come back with a V1 plan. Send me a document, a memo, something concrete. It's incredibly valuable to have team members who can say, “I heard you – here’s how I would change our strategy in response.”

How to build your change muscle

Most people aren’t born with these capabilities. Here's how to practice:

Make daily pivots. When your calendar gets blown up or a plan changes in some way, use it as practice. Instead of complaining, give yourself 10 minutes to figure out how to react. Be intentional and write down your new plan or schedule. Use these little pivots as training for the bigger ones.

Join the change. When your company announces a new initiative, volunteer to be part of the new team. Don't be on the sidelines asking, “Why did they do that?” (or worse, saying, “Nobody told me!”). Be in the room figuring out what happens next.

Build your change radar. Pay attention to what's shifting in your industry, your company, and your role. The people who get blindsided by change are usually the ones who weren't paying attention to the signals. Follow or subscribe to relevant insights (role or industry), talk to customers or other stakeholders, notice what your leadership team is focused on. Remember, change can sneak up on you.

Practice the five-hour rule. When something big changes, give yourself exactly five hours to process it emotionally, then switch to problem-solving mode. This short timeline (less than a day) forces you to move from reaction to action quickly. And if you really need more time – like overnight – then commit to waking up the next day and working on your new plan.

My advice

In this moment of AI acceleration, I think people are similar to companies. We have incumbents – well-established, experienced contributors, and we have challengers – less-experienced, but fast-moving and innovative newcomers.

The challengers have nothing to protect (turf, title, corner office) and are much more comfortable with the change – and will in fact try to accelerate it. Change makes them more valuable.

So, if you are a challenger, push your advantage – propose change, in the form of new ideas and ways of solving problems.

And if you are an incumbent, don’t abandon your experience, but keep pace with change. As a minimum, I want you to practice the “5 hour rule” and be the incumbent that absorbs change quickly, with no freakout. And be the first to propose the way forward – in writing.

If I can do this, you can too!

Have a great week,

Greg